GB1068451A - Novel dihydro-dibenzocycloheptene derivatives and a process for the manufacture thereof - Google Patents

Novel dihydro-dibenzocycloheptene derivatives and a process for the manufacture thereof

Info

Publication number
GB1068451A
GB1068451A GB424/66A GB42466A GB1068451A GB 1068451 A GB1068451 A GB 1068451A GB 424/66 A GB424/66 A GB 424/66A GB 42466 A GB42466 A GB 42466A GB 1068451 A GB1068451 A GB 1068451A
Authority
GB
United Kingdom
Prior art keywords
formula
group
halogen atom
prepared
compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB424/66A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
F Hoffmann La Roche AG
Original Assignee
F Hoffmann La Roche AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by F Hoffmann La Roche AG filed Critical F Hoffmann La Roche AG
Publication of GB1068451A publication Critical patent/GB1068451A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel compounds of the Formula I wherein R1 represents a hydrogen or halogen atom or a hydroxy or acyloxy group and R2 represents a hydrogen atom, or R1 and R2 together represent a keto group; R3 represents an unsubstituted or substituted amino group and R4 and R5 each represent a halogen atom or a trifluoromethyl, alkyl, alkoxy, alkylthio, acyl, sulphamyl or alkylsulphamyl group and the broken lines indicate that the substituent attached thereby is optional; and ketals and acid addition salts thereof, are prepared by reacting a compound of the Formula II wherein R6 represents a hydroxy group, R7 represents a hydrogen atom and R8 represents a halogen atom or R6 and R7 together represent an oxo group or R6 and R8 together represent an oxygen bridge, or a ketal thereof, with ammonia or an appropriate amine and, if desired, converting the product by acylation of the 10-hydroxy group if present or replacement of the hydroxy group by a halogen atom; acylation at any unsubstituted or monosubstituted amino group; or ketalation and, if desired, converting a resulting free base into an acid addition salt. Compounds of the Formula I where R1 represents a hydrogen atom are prepared by reductive dehalogenation of the corresponding compound of the Formula I wherein R1 represents a halogen atom. Trans-compounds of the Formula I are converted into cis-compounds of said formula by methods known per se. <FORM:1068451/C2/1> <FORM:1068451/C2/2> Dibenzocycloheptenones of the Formula II where R6 represents a hydroxy group and R8 represents a halogen atom may be prepared by treating the corresponding dibenzocycloheptenones with an agent which yields a hypohalous acid in the presence of water or by treating the corresponding compound where R6 and R8 together represent an oxygen bridge with a magnesium halide. Dibenzocycloheptenones of the Formula II where R6 and R7 together represent an oxo group and R8 represents a halogen atom may be prepared by oxidation of the corresponding compounds of the Formula II wherein R6 represents a hydroxy group. 10,11 - Epoxy - 10,11 - dihydro - 5H - dibenzo-[a,d] - cyclohepten - 5 - one may be prepared by the action of hydrogen peroxide on 5H-dibenzo-[a,d]-cyclohepten-5-one. d,l - cis - 2 - Phenyl - 3a,12b - dihydro - 8H - dibenzo - [3,4,6,7] - cyclohept - [1,2-d] - oxazol - 8 - one hydrochloride is prepared by reacting d,l - trans - 10 - hydroxy - 11 - benzamido - 10,11-dihydro - 5H - dibenzo - [a,d] - cyclohepten -5-one with thionyl chloride. Therapeutic compositions with antidepressant properties, in the form of tablets, dragees, capsules, solutions, emulsions, suspensions, salves and suppositories, for oral, parenteral and topical application, comprise compounds of the Formula I and ketals and acid addition salts thereof in admixture with a compatible pharmaceutical carrier.
GB424/66A 1965-01-08 1966-01-05 Novel dihydro-dibenzocycloheptene derivatives and a process for the manufacture thereof Expired GB1068451A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH23265A CH464894A (en) 1965-01-08 1965-01-08 Process for the preparation of dihydrodibenzocycloheptene compounds

Publications (1)

Publication Number Publication Date
GB1068451A true GB1068451A (en) 1967-05-10

Family

ID=4182293

Family Applications (1)

Application Number Title Priority Date Filing Date
GB424/66A Expired GB1068451A (en) 1965-01-08 1966-01-05 Novel dihydro-dibenzocycloheptene derivatives and a process for the manufacture thereof

Country Status (10)

Country Link
BE (1) BE674704A (en)
BR (1) BR6576113D0 (en)
CH (1) CH464894A (en)
DE (1) DE1543037A1 (en)
ES (1) ES321534A1 (en)
FR (2) FR1464312A (en)
GB (1) GB1068451A (en)
IL (1) IL24852A (en)
NL (1) NL6600200A (en)
SE (1) SE343052B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3457264A (en) * 1965-07-06 1969-07-22 Farmochimica Cutolo Calosi Spa N-(5h-dibenzo-(a,d)-cyclohepten - 5 - one-11-yl)-piperazines and method of preparing the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3457264A (en) * 1965-07-06 1969-07-22 Farmochimica Cutolo Calosi Spa N-(5h-dibenzo-(a,d)-cyclohepten - 5 - one-11-yl)-piperazines and method of preparing the same

Also Published As

Publication number Publication date
DE1543037A1 (en) 1969-09-11
ES321534A1 (en) 1966-11-01
BE674704A (en) 1966-07-04
FR1464312A (en) 1966-12-30
BR6576113D0 (en) 1973-09-06
SE343052B (en) 1972-02-28
FR5376M (en) 1967-09-18
NL6600200A (en) 1966-07-11
IL24852A (en) 1969-12-31
CH464894A (en) 1968-11-15

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